The Temporary Secretary
by ChickenGoesMoo
Summary: Gabriel is the head of a temp agency… sort of. After a year of work, the last secretary for the law firm Winchester and Sons decided to run off with a guy from the mailrooms. Normally it wouldn't be a problem, but Dean, the man requiring said secretary, has very specific requirements for the job. And Gabriel knows just who to rope into doing it: His estranged lil' brother, Castiel.
1. Chapter 1

Gabriel growled when he opened his emails. It was the seventh email he had received this week from the offices of Winchester and Sons. Apparently, their last secretary had been calling in sick for the past week, and they had hired her through Gabriel. He ran a very good business, and prided himself at being able to find the perfect person for a position, no matter the job. And he had been asked to find people for extremely odd jobs before, but he was appreciated for his promptness and discretion, which is why he was so well known in certain circles. He didn't discriminate, and he had great contacts, and even if he didn't know someone for a job, he knew someone who knew someone. He always delivered, and his success rate at finding a perfect match for the jobs was nearly flawless.

This particular match was probably the worst failure he had ever made, and the Law Firm he hired the secretary for didn't seem to be too keen on letting it go. Sure, the girl was smart, and she looked good on paper, what with plenty of experience and a high word per minute count. She came with very high praise, and she matched all of requirements. It was the practical application that was lacking. Something no resume will ever say was if that person had a tendency to be flighty.

And, apparently, Becky was.

Dean Winchester, her boss and a name partner at his father's firm, found out via social media that she had been in Hawaii the entire time with their mail clerk. She was getting married on a last minute whim, all the while calling him every morning pretending to cough up a lung.

It would have been hilarious to Gabriel if her boss wasn't one of the cities best lawyers, possibly on par with his own brother, Michael, who worked for a rivaling firm. As it were, the man found a loop in the contract he used to hire the girl, and if he didn't find a replacement soon, Gabriel would possibly be sued. Of course, Gabriel knew Dean Winchester had better things to do with his time and money than sue the agency that helped him find a secretary. Still, it would be bad for business if he didn't come through for a paying client, and Gabriel really didn't want to deal with all of the bad press it would give him if word got out.

On the other hand, finding another secretary that was the perfect match for a finicky lawyer at such short notice was putting him in a bad way. After all, he had about forty other clients who needed anything from personal trainers and cooks, to baby and dog sitters. He didn't have the time to find a—

Gabriel rustled through his documents, searching for the requirements one Dean Winchester made for his secretary several months back.

The bullet points were quick, easy, and to the point.

 _Secretary prerequisites:_

 _100 wpm typing speed minimum_

 _must speak at least one foreign language fluently_

 _typing, shorthand and audio transcription skills_

 _word processing and spreadsheet skills_

 _administration skills_

 _excellent grammar and spelling_

 _Discretion in handling confidential information_

 _making appointments and keeping diaries_

 _Skill at using short hand during meetings_

 _typing letters and writing emails_

 _updating records in databases and spreadsheets_

 _dealing with phone enquiries and emails that reflect the company's best interest_

It was all generic stuff that he usually dealt with. Very simple to find a good secretary with those kinds of requirements.

It was the 'preferable if' category that was the hardest quota to fill. Apparently, the impatient, narcissistic, asshole of a lawyer was more than a little superficial, which should have been obvious to anyone who looked at his extensive sports car collection. It made Gabriel laugh the first time he read through it. Because it was obviously a joke!

Except it wasn't. This man was deadly serious. Which made it all the more hilarious in Gabriel's mind. He always loved a challenge. And he always loved to deliver the perfect employee, just to prove he could.

 _Preferable if the secretary_

 _Is Young_

 _Has a sensual voice to answer the phone with and a good, disarming smile to greet people with at the desk._

 _Looks good in a dress and heals. Will probably be joining me at certain events, and must be able to make a good impression at my side._

 _Is able to keep a professional distance with opponents and clients while still being able to manipulate the competition into letting their guard down around them._

 _Has A great poker face_

 _Has Blue eyes._

 _Is Willing to spend late nights at the office and work long hours and hard tasks with minimal praise._

 _Is Willing to submit self to my occasional bad temper, and odd whims when I win cases or hit a temporary roadblock._

 _Is shorter than me._

Even rereading it made tears of laughter come to his eyes. It was more like he was looking for the perfect wife rather than a secretary. And it took Gabriel the better part of a month to find the first one. And amusingly enough, he did find the perfect wife, just not for Mr. Winchester.

Oh the irony.

He scanned through the subtly threatening email with dwindling interest, flipping back to the required skills list, then the preferred list when he was really bored and needed a laugh. He knew that if he ever met the man in person, Dean would more than likely not hesitate to rip him a new one, but seeing as how emails left obvious paper trails, he doubted the lawyer would risk threatening too much more than Gabriel's money and job in emails. And, seeing as how he ran his business out of his home, and nobody but his brother Michael knew where to find him, it was doubtful anything too traumatizing would come from this.

Obviously the corporate snob was having a baby panic attack after going two weeks without having a hot little thing at his front desk to help change his diapers and wipe his nose.

He read through the list again. Gabriel was amused to note that while the entire letter was obviously typed with a sexy woman secretary in mind, no gender specific terms were made. With how irritating the lawyer was beginning to get, perhaps it would be fitting if he set the jerk up with a man fitting the description. Just desserts and all that jazz.

Of course, he wouldn't put his worst enemy at this douche's mercy.

Gabriel sighed, buzzing his lips together, skittering his fingers across the keyboard without really pressing anything, but enjoying the obnoxious tapping it made anyway while he thought.

Coming up blank after not even trying, but convincing himself that he put enough effort into it for the day anyway, he popped open a separate browser. Boredom, and maybe a little bit of nostalgia at the thought of pranking someone made Gabriel's fingers walk their way across the keyboard to an old Google account he helped his little brother set up ages ago, back when they were still on talking terms.

 _Daddyslittlestangel at Gmail dot com._

Well, obviously, seeing as how he was the one who helped his little brother make the account, he was the one to name it. And it was amusingly fitting if Gabe did say so himself. It wasn't like he was doing anything bad, really. It had been years since Gabriel had left the house without looking back, and by now Castiel was an adult, probably graduated from some

University with a degree under his belt and a steady job. Maybe even a wife and kid. Obviously a professional like that wouldn't still be using such an embarrassing email address. And if he was, he would have at least changed his password by now.

Gabriel scrolled through the inbox, expecting to find one of the old emails he sent Castiel a few years back to be sitting there, unopened. He most definitely didn't expect to find what was sitting there, sent not one day ago to the account.

 _'Saint Mary High School end of year party! RSVP!'_

Gabriel clicked it, thinking it must be some spam sent to a dead account.

Obviously that was not the case.

After three hours of digging, and a lot of laughter, Gabriel had gone through most of his little brother's old mail, hacked into Castiel's iCloud, Facebook, work email, and so much more. Posted a face of himself on his brother's Instagram, which was sadly inactive, and stalked through all of his little brother's posts since he first created a Facebook account. Heck, he was so bored that he even added himself on as a contact in Castiel's iCloud, so if he backed up his phone every night like Gabe suspected the rule following little brat of a brother would, he would randomly find Gabe's number there.

Gabe was really starting to have fun digging up dirt on a brother he hadn't seen in years, but appeared to have grown into a rather attractive young man without his influence. Apparently, Castiel had left home, gone to college, and decided that, despite being bullied in high school, he would use his perfect grades to earn a degree to go back there and help teach the brats that once tormented him. That, or he decided that because they tormented him, it was his time to get a little pay back by ruthlessly drilling Latin into their minds for an hour a day. He was so amused at his little bro's choices in life that he almost completely forgot his previous dilemma until his phone dinged.

He looked down at his phone, a dark frown replacing his nostalgia induced grin. It was another email from Dean Winchester.

Gabriel sighed, and picked up his phone, leaving a Facebook photo up on his computer monitor of Castiel standing rather awkwardly in a sea of graduating high school girls, one of whom looked as though she was grabbing Cas's butt by the strained look of horror he was expressing through a forced grin. He knew there was a reason he made fun of that awkward little geek. He scrolled through the email swiftly. He would decipher what was happening in the picture in a moment.

He reached the end of the email, barely containing his frustration. Man, this dude was a giant dick! Gabriel was literally working as hard and fast as he could here! You can't rush perfection!

All Dean stressed throughout the entire email was that he absolutely needed someone to start right away. He didn't even care about their skill set, stating that they could _'be a brain surgeon for all he cared_ ,' just so long as he had someone to field his calls for a few weeks while Gabe worked on finding someone more permanent.

Gabe paused when he read that, his mind turning it over, objectively thinking through his options. There was Monique, but she wasn't really free for another week. And there was…

A wicked grin warped his features as Gabe's eyes drifted to the photo of Little Castiel grinning awkwardly at him from the monitor. He couldn't stop himself from laughing.

"Blue eyes," he stated with a grin, and jumped at the computer, pulling up old emails and using his contacts to get a hold of college records. Within moments he was composing a resume from what he could find of his little brother's qualifications matching the position.

Five hours later, he sent out his very detailed response.

 _Hey, buddy!_

 _Looks like I found you your temporary secretary! Sadly, they have a seasonal job, but they should hold you off until I find you something else. Take a look and let me know how you feel about it? It's all I can scrounge up short notice, but hopefully they will do nicely._

 _Name: Castiel Novak_

 _Hight: 5'11"_

 _Eye color: Blue_

 _Typing speed: 140 wpm_

 _Language skills: has taken four college level courses in Latin and Japanese, and three years of French and Spanish._

 _Has extensive spreadsheet experience, and is know to work long hours while being under appreciated and under paid._

 _Administrative experience._

 _Fields email, and phone calls daily._

 _Respectful of privacy._

Gabriel had to force himself not to tack on the little tidbit about how he was certain that Little Cas looked good in a dress and heals.

What? He was an older brother. Of course he had his fun playing dress up with the littlest Novak. He had been… what, Eighteen when he convinced Luke to hold their baby brother down while he forced a wig and makeup onto their traumatized little sibling when dad and Michael left them in charge of the house one night. Which would have made Castiel… eleven? Maybe twelve? Hey, people could call Gabriel a great many things, but good big brother was not one of them.

He still looked upon the memory fondly, remembering having Luke pose with the slightly bruised, dress toting, stiletto wearing little Cassie. The look of resigned acceptance on his little brother's face in every one of those photos had made him laugh even harder than when he found his brother burning the photos, and trying to shred the negatives a week later.

It didn't even take Dean an hour to respond.

 _She sounds perfect! When can she start? And Novak? Is she related in any way to you or your brother Michael? You can understand how that might pose as a problem._

 _Dean Winchester_

Gabriel smirked. Perfect! He couldn't be happier with his father right now for giving his little brother such a authentic name as Castiel. Heck, half of the substitute teachers in school never believed Cas when he raised his hand to that name during morning attendance. They all thought he was joking.

Gabe quickly typed out his response.

 _Cas is a—_

He paused, trying to think how he could describe the relationship they shared without outright admitting it. Because nobody wanted to admit that they had a little sibling that they hadn't seen in years, especially when your older brother worked at a rivaling firm. Something like that coming out definitely wouldn't be good press for Michael. In fact, it would probably be best if Michael not find out about Cas working for a competitor in the first place. He was mad enough when he found out how Gabriel had aided them in hiring a few workers.

 _—distant relation._

Perfect description of their relationship! He wasn't lying, because Castiel was a relation, and he was very distant considering he lived nearly on the other side of the United States.

He continued typing out his full response.

 _I am pulling a big favor to get Castiel here, who lives in another state. I will be out a guest room until I find someone more suitable for the position, but I like to make sure all of my clients are well cared for._

Gabriel hit send, buzzing with excitement at the idea of pulling one over on this jerk, even if it was a minor thing. And on the plus side, it would give him a chance to catch up with his little brother for the first time in ages.

His phone buzzed not moment later.

 _Thank you for your speed and the impeccable service of going above and beyond. This secretary looks like a match made in heaven, and I will be sad to part with her if she is anything like the description you sent me portrays, but I am sure you will find someone even better as a replacement._

Gabriel nearly choked on his own laughter. Now the man was trying to butter him up!? The damage was already done. He already went and ticked Gabe off. No takesy backsys.

The email continued.

 _I apologize for my rude behavior earlier this week. My old secretary seems to have taken my date book with her on her extended vacation, and I have been scrambling to make up for lost meetings. Thank you for being so understanding. And if you find yourself in need of your guest room any time in the near future, I would be glad to offer one of my own guest rooms for Castiel's use._

Gabriel snorted at the last sentence. "I'm sure you would," he muttered to himself. "You horndog."

Gabriel stretched, pushing away from his computer absently, scratching his stomach and yawning before looking at the time.

He had been up all night messing on the computer, hunting down info to prank a big time lawyer by bating him with his little brother's information.

Was he really that petty?

He shrugged to himself, opening up the refrigerator and pulling out a popsicle.

All the was left was to call Cas and convince him to take the job. Which probably wouldn't be easy, but he had the power of email hacking on his side today. Surely there was some dirt that would make Castiel do anything he wanted.

He returned to his computer with a smile, sitting himself down and taking a few delightful spins in his wonderful swivel chair before getting comfortable, scrolling through a few of the recently deleted emails, eyes landing on a innocent looking message from a Dr. Ellicott.

This looked promising...

* * *

Castiel knew he shouldn't have picked up the phone. The moment he saw the impossible name on the cover of his phone- no, the moment he heard the flamboyant ringtone, he knew he should just pretend that he was dead. Playing dead had worked for the past eight years, so a few more unanswered calls wouldn't ruin his already nonexistent familial relations. It was his first day of summer vacation anyway, and he was not going to spend it as Gabriel's source of entertainment like he had for his first fifteen years of life. He did enough of that when he was younger, and he was not about to do that again.

So, despite feeling slightly guilty, he reached out of the warmth of his comforter and pressed the side button, silencing the ringing for the time being.

He furrowed his brows at the phone irritated when he realized that, despite the phone having stopped ringing, the front display was still lit up, and the name 'Gabriel' still flashed across the screen a few more times. Castiel tried to close his eyes, but the light of the electronic screen was too bright to let him lull back to sleep.

He rolled onto his other side, pulling the covers up over his face a little bit, sighing in happy contentment when he found himself slowly fading into a dream.

 _"BEEP! BEEP! BEEP!"_

And that happy little dream scape was shattered the moment the phone decide that it should inform him, incase he some how forgot within the last ten seconds, that he had missed a call.

Castiel clenched his eyes tighter, trying to hold on to that last strand of sleep before he was forced to wake up for the rest of the day. It took a couple seconds, but eventually he relaxed. All of the feelings of guilt revolving around not picking up a call from one of his practically estranged family members was blocked out as a quiet huff of air pushed its self out between slightly parted lips. It almost sounded like a snore, which may have been brought on by congestion gifted to him by one of the kids that he was forced to handle the day before. The silly girl was obviously sick, but decided she couldn't miss the last day of school and her final chance of the year to prove how much undying devotion she had for her darling "Mr. Novak." Even if that meant getting him sick by leaving an anonymous, germy letter on his desk covered in hearts and snot.

She was honestly one of his better students, which made it all the worse considering he didn't know if she was actually good at Latin, or was only trying in his class because she wanted him to notice her. She was failing in all of her other corse work.

 _"BEEP! BEEP! BEEP!"_

Castiel couldn't hold back the near growl he made when his eyes snapped open and he rolled back over to stare at the offending piece of technology.

 _'One missed call from Gabriel."_

 _'One new voice message.'_

He sleepily reached out for the phone, accidentally knocking it off his bedside table in the process. He considered going after it, but that seemed like too much effort. And he could probably fall back to–

 _"It was the— HEAT of the Moment~!_

 _Telling me what you–"_

In a flurry to get to the phone and make it stop for the fourth time that morning he threw his hand over the edge of the bed, grasping in the direction of the obnoxious sound, and misjudging his reach.

His arms and legs flailed uselessly when he attempted to regain his balance on the edge of the mattress, his torso falling off the bed, head colliding with the floor just inches from where the phone was buzzing innocently.

Castiel twisted himself around and opened his eyes, looking at the phone like it betrayed him worse than Caesar was betrayed by Brutus.

In fact, it was such a good comparison to Castiel's sleep depraved mind (which, honestly, anything sounded agreeable to a sleep deprived Castiel) that he couldn't stop the 'Etu Bruté?' from spilling out of his mouth dramatically.

He kicked lazily at the sheets for a second until they untangled from his legs, letting the rest of his body fall onto the floor, uncomfortably angled against the bed frame.

The phone stopped ringing for a moment and Castiel just stared at the ceiling despondently. He considered for a second if he should call Gabriel back. He hadn't talked to his brother for nearly eight years. In fact, he hadn't talked to any of his family for a very long time. Maybe something terrible had happened? Maybe his dad was sick. Maybe Luke finally picked a fight with the wrong person. What if Michael was in a car accident?

Castiel was interrupted from his dreams— or… nightmares? Yes, definitely nightmares. Because he totally would not be happy to find out if his father was sick. And it would be very upsetting if one of his older brothers met an untimely end. Very upsetting indeed. So upsetting he would be hitting a bottle of champagne in celebra— mourning! Obviously he would be mourning!

Well, anyway, he was interrupted from his thoughts by the sound of Gabriel's ring tone going off again by his head again.

So, Castiel reached for it. Because calling once after several years could simply amount to a checkup. Leaving a message was worry. Calling twice consecutively and leaving a message again was a bit panicky. Calling three times? Something was seriously wrong.

Of course, one thing slipped Castiel's sleep fogged mind as he reached for the phone. Maybe it was because of the years he hadn't spent in touch with his brother Gabriel, but he severely overestimated how much actual growing up his brother had done in that time, and misremembered how irritating and child like Gabriel could be if you tried to ignore him. Maybe, if he had thought about it for a moment longer he would have never picked up his phone. Maybe he would have still been sleeping with his phone now turned on silent.

Sadly, Castiel didn't make good choices when he was half awake. Or half asleep, as it were.

"What do you want, Gabriel?" Castiel grumbled, trying to make a comfortable nest on the ground with the comforter. If possible, his voice was even deeper than usual, what, with a slight cold coming on and his over all not being awake coming into play.

The irritating but oh so memorable gale of laughter that met him on the other end of the line made Castiel instantly cringe and regret his decision to answer the phone. Just the sound alone was enough to bring so many bad memories to the forefront of his mind.

"Little Casi! Is that really you?" Gabriel jeered. "Haven't talked to you in a while. Some how, it doesn't surprise me that you became a smoker. You were always the anxious one. How many a day are you going through?"

Castiel bit back a huff of irritation. "I don't smoke. Certainly not after I spent that entire night getting my stomach pumped when I was five because Luke convinced me to eat an entire ash tray of cigarette butts, and definitely not after you 'accidentally' locked me in a closet with a lit bong over night when I was eleven," Castiel grumbled, irritation flaring at the old memories, suddenly remembering why he hadn't been in contact with his brothers in so long.

"There is no way that is your real voice, kiddo," Gabriel laughed, ignoring his brother's passive aggressive state. "Last I talked to you, your voice was all nasally. Now, every time you say something it's like I am watching that shitty batman movie all over again!" There was a slurping sound on the other end of the line, and Castiel realized that Gabriel must still be going through his love affair with candy. And Gabriel was supposed to be eight years older than him?

"I haven't exactly seen nor spoken to you since… my junior year of high school?" Castiel answered back, trying to angle his body enough so he could see the clock above his bed, completely forgetting that he had his phone in his hand. "It's early, and you woke me up. What do you want so bad that forced you to call me thrice? And at," he forced himself onto his knees and looked over at the clock, only to realize he must have unplugged it from the power strip in his fall from the heavenly confines of his bed, "what ever 'o'clock in the morning this is?" He rubbed his eyes.

Gabriel tittered, "What? Can't I just call to check in on my favorite little bro every now and again?"

"I am your only 'little bro,' as you call it." Castiel grumbled back, standing and making his way into the restroom to splash some water on his face. He really needed to wake up if he was going to have a conversation with Gabriel. "Hurry up and tell me who died so I can carry on with my life, if you will."

Gabriel, irritating as ever, actually laughed at that. "Nobody died, silly! Knew Saint Mary's was on summer break, and figured you could use a break from all of that Latin and stuff."

Castiel had a sharp intake of breath just as he went to splash himself, partially soaking his phone, and nearly choking on the water. It took him a moment to recover, and by that time his voice was even more raspy than usual.

"How do you know about that?" He gasped in panic.

There was a confused silence on the other end. "I don't know, batman? Know what?"

"My job?! How do you know where I work? How do you know my phone, for that matter?!" Castiel forced out, pulling his head away from the receiver to look at the contact name. "In fact, how do I even have your contact in my phone?"

"Easy!" Gabriel chirped, "I hacked into your iCloud a bit ago and added my contact. You really need to change your passwords, and maybe get a new email. It's the same one you have had since you were thirteen!"

Castiel took a deep breath to steady himself, and when the room was still spinning after that, he quickly sat down on the toilet, nearly falling in when he remembered that he left the lid up last night. "Gabriel, that isn't normal behavior," Castiel hissed. "That verges on stalking!"

"Come on! Dad use to monitor your internet access all the time," Gabriel argued. "I'm just looking out for you! And it wasn't like you were answering any of my emails. I just wanted to check that you were getting them okay."

Castiel sighed, burying his head in his shaking hand. It could always be worse, he guessed. It could have been Luke or Michael that was hacking into his email and iPhone. Gabriel was the most innocuous of his siblings that he could remember. Perhaps this wasn't the end of the world like he thought it was. "How did you expect I would handle it? I'm not exactly happy with you. When you left… everything fell apart."

Gabriel went silent for a moment. "You make it sound like it was my fault, kid. Michael and Luke had had it out for each other. It would have happened eventually."

Castiel nodded to himself, trying to fight back his irritation. He knew what Gabriel was saying was true, but it still didn't make running away right. Then again, wasn't that exactly what he was doing?

"I guess," Castiel conceded. "It was hell after you left though. Have you talked to either of them recently?"

"I have talked to Michael. I actually do business for him occasionally. He took over dad's firm out here in New York before he retired to God knows where. I am kinda like a corporate head hunter of sorts, which is part of why I called you, actually."

Castiel's brows furrowed again. "What happened to Luke?"

"Don't know. Hopefully where ever he is, there isn't a stick up his butt as big as the one up Michael's. All work and no play makes Michael a dull boy, you know what I mean?"

Castiel frowned. "Not really," he said, trying to figure out if that was a movie reference or something. He knew he heard it before.

"Hm. You will figure it out eventually," Gabriel responded. "I am flying you out here. I have come across a bit of a hiccup, and I am calling in a favor."

"From who?" Castiel asked blankly. Because really, who owed Gabriel anything?

"You, silly! I need a filler secretary for this ass-wad of a firm. Apparently, the first girl I found for them was perfect, but she may or may not have run away with the mail clerk a couple of weeks ago, and they keep on crawling up my ass about it! Not my fault the girl fell in love, is it?"

There was a pause, and Castiel guessed that it was not a rhetorical question after a few moments. "Ummm… no?"

"Exactly!" Gabriel burst out, then took a deep breath.

"I don't know of any secretaries looking for a position, but I will call you if any come to mind," Castiel answered slowly, not liking the direction this was going, and not really knowing why.

"See, that won't work. He is really really picky about who he lets work for him, and honestly, I can find him someone good if he gives me a moment to go through all of my contacts, but until then, he will be out a secretary, and you know how all those big lawyer types are—"

"Not really."

"— their heads are so far up their own asses that they can't wipe their own noses without a secretary. All I need is a temporary secretary. Someone who will be okay with doing a job for just a month or two until I find someone permanent to take their place."

"Just how do I equate into all of this?" Castiel asked slowly.

"Casi, don't play coy! You are the best person I could think of for the position! You are fluent in several languages, you are super organized, and you can type 140 words per min? Perfect! You can take care of that big baby until I find someone better and more permanent, that way I don't have a hot headed lawyer threatening me every single day while I am trying to do my job for my other forty well paying clients."

"I am not a secretary." Castiel stated dumbly.

"Hah! Obviously! You are a teacher during summer break. It's not like you do anything during summer anyway? Right?"

"Actually I—"

"Exactly my point. And the plus side is, you can crash on my couch while you are here! We can catch up and—"

"No, Gabriel."

"—just be bros! Wait, what?"

Castiel tried to calm his nerves. He never was very good at standing up for himself. Especially when it came to his brothers. It always ended badly. "I said no, Gabriel. I have a life. I have lesson plans to form, angry parents to talk to, and field trips to plan. I have not even heard your voice for the longest time since this morning, and you want me to drop everything? For you, of all people?" Castiel swallowed nervously. Gabriel was being eerily silent. He was always the most dangerous when he was quiet. He was a loud person in general, so when he wasn't talking at all, it always set Castiel on edge. But he wouldn't back down. Not on this one. "No."

"Well, this is awkward." Gabriel muttered in a peeved voice.

"I am sorry—"

"Oh, no. Not about that." Gabriel interrupted, his voice had a sharp edge to it that made Castiel wince. "I was just reading a few of your emails."

Castiel felt all of the blood drain from his head. It was hard to breath for a moment, and it felt like someone just passed over his grave. "Gabriel, stop! That is my personal—"

"Your therapist really rambles, doesn't he?"

Castiel was standing now, shaking the phone, and running a nervous hand through his sleep ruffled hair. "Close that email right now!"

"Oh my!" Gabriel crooned. His voice wasn't harsh now that he had Castiel on the edge. It was light, mocking, and if Castiel hadn't known any better, he might have sounded caring. "Remember that little prank I pulled on you when you were thirteen? Apparently I wasn't too far off base, was I?"

"I swear, Gabriel!" Castiel pulled the phone away from his face slightly, glaring at the receiver as if it were the man in question, shaking a threatening fist at it. Not like he would actually do anything if he could. Castiel abhorred violence, but it was starting to sound pretty tempting at the moment. He guessed family could do that to a person. "If you don't shut up right now—"

"Hmm… you are right. This seems pretty serious, and nothing to joke about," Gabriel relented, and Castiel let out the breath he had been holding. Obviously Gabriel wouldn't use that against him, he wasn't that cruel, was he? "Perhaps I should forward it to dad and Michael. I am sure they would love to see how you are holding up after all these years. They must worry about you!"

His heart stopped. His breath was forced from his body so fast that it felt like a physical blow. Castiel was on the verge of tears, and he wasn't sure if it was rage or fear that was causing them. "Fine," he croaked, teeth clenching. "I'll do it."

There was that irritating laughter again. "Knew you would come around to see my way of thinking eventually, lil bro." Gabriel cheered.

"I hate you." Castiel turned, and rested his free hand and head against the wall, pressing his now feverish forehead against the tiles in hopes that it would help him calm down.

It didn't.

"Of course you do! We are family after all. I will text you with the flight confirmation in a bit." Gabriel continued, completely enjoying the sound of defeat in his brother's voice. "For now, get some rest. You sound terrible!"

With that, the line went dead, and Castiel just stood there for a moment, wondering if he could some how convince himself it was all a dream if he fell back asleep.

It didn't really matter anyway. He couldn't fall asleep after that if he tried.

* * *

Dean was sitting next to his phone, desperately awaiting Gabriel's response for when his new secretary could start. At this point he really didn't care who it was. For the past week and a half now he had been borrowing his brother's secretary, trying to manage his own meetings, take his own notes, keep an eye on all email correspondents, and answer all calls while juggling his own case load. It was nearly impossible without the help from Meg, and even then his cases were taking a major hit. He couldn't focus enough on the small details of the case with so many other things going on. He was barely able to keep his head above the water.

He knew he shouldn't have taken his frustrations out on Gabriel. It wasn't his fault that the previous secretary ran off. But it was hard not to get angry at someone!

He smiled and looked down at the email again describing his new secretary. She was the jackpot from what it sounded like. Sure, she was a little tall for his tastes, but that was fine. He could handle it if she was a little leggy, especially if she wore short skirts.

And what kind of name was Castiel, anyway? Was she foreign? It sounded exotic, and it was a bit of a mouthful. Maybe she went by Cassie? Dean rather hoped she didn't. He had an ex girlfriend that went by that name, and he didn't like the reminder. He'd probably just call her Cas. If she didn't like it, oh well. He only had her for a couple of months before she went off to her other job… whatever that was.

Hopefully she was as loose as the last secretary. Becky had slept through nearly the entire staff before settling with the mail man, who had been trying to get her attention the entire time. It was a little sad to watch, but she was always game when Dean needed to celebrate a big win, and he was never one to say no to a good time. On top of that, she obviously didn't seem to want a serious relationship with anyone except his brother, who was very much not interested in the somewhat stalkerish woman who had been stealing his pens.

Dean paced over to the window of his luxurious penthouse suite, which happened to consist of the entire sitting room wall facing the sunset. Oh, the memories he had in front of this window. He was on the thirtieth floor, and he could see a good portion of the city from his perch. Thankfully, the city couldn't see him back very well. He often brought his conquests here, including Becky. The view and a glass of whisky would make them putty in his hands.

And this new secretary was only going to be there for a month, maybe two at most? Perfect grounds for a quick hookup with no strings attached.

If she really was verging on six foot, she must have legs for days. Lovely, long legs that would wrap around him perfectly while he pushed her against the glass wall of his suite.

He sighed. He was drunk, and he had just ended a long week, full of tension and pent up frustration. He deserved this. He was owed a bottle of his best scotch. And if the hand that wasn't currently attending the glass of alcohol just happened to find its way to the crotch of his pants, palming what was eagerly waiting there, then so what? This was the first moment of relaxation he had gotten all week.

He imagined what she looked like. His fantasy secretary had long, dark hair that flowed down around her shoulders in slight waves, accentuating her breasts and cleavage. She would have deep, expressive blue eyes that would lose focus when he brought her close, or caught her off guard with something extremely sexy. Maybe she would says something sexy in one of those languages when she was lost in throws of passion. Dean didn't care what she said, just so long as she said it in that sexy, husky voice some women got after being thoroughly kissed.

Dean let out a frustrated grunt when his phone vibrated in his pocket, making him subconsciously thrust at the unexpected stimulus, interrupting him from his fantasy with a response he had been waiting for all night.

 _Your new secretary will be available to you on Monday, at noon to settle in and learn about the new responsibilities of the job. And please be gentle. Castiel is not a secretary by trade, so there will be a little bit of a learning curve, but I am sure you two will manage._

Dean frowned, and sent out a follow up message without even pausing to think about if it was appropriate or not.

 _What is Castiel's regular occupation?_

Dean waited for the response. He didn't need to wait long. Gabriel emailed him back instantly, quick simple and to the point.

 _High school Latin teacher. Like I said, a bit of a learning curve, but it's only a temporary fix. It's not ideal, but I'll find someone more suited soon and this should keep you held over till then._

Dean knew that hearing that his new secretary was a school teacher should have upset him. The thought of a 'learning curve' should have worried him.

Should have. But Dean was a little too drunk to think about that part of the equation. All he could see was 'high school teacher,' and his pants began feeling a little tighter. The room began to feel a little warmer.

And then Dean decided that he would retire to his bedroom for the night, with nothing but his imagination, a glass of scotch in one hand, and, before long, his other hand would be wrapped around something else.

Maybe if he played his cards right, his sexy little school teacher/secretary would help him relax next time.

He just hoped she would be able to live up to his expectations. Because he had a lot.

* * *

Writer's Note:

This is a ChickenGoesMoo work in progress. I am not often on , but I do have a more regularly updated account on ArchiveOfOurOwn that you can check out for other stories by the same name. I will try to post the remaining chapters I have done of to this work within the next several days. I just wanted to see how the two different sites worked, and see if cross posting my work on another site was a good idea after it was suggested to me by a friend.

Let me know what you think, and or check out my other account, also ChickenGoesMoo on ArchiveOfOurOwn


	2. Chapter 2

Castiel didn't know what he was expecting to see when he got off of the plane at eleven p.m. the evening before his first Monday of a wonderfully student free summer break.

As a child, he was often tormented by his much older siblings (and apparently he still was), which was partly why he went to a college out of state in the first place. It was also why he stayed out of state and as far away from his psychotic relations as possible. He had gotten tired of the laxatives sprinkled over his lunches at school and being plastic wrapped to his own bed.

Don't get him wrong, he loved his family, he just decided that, after Luke 'accidentally' lit him on fire and pushed him down a third story fire escape, he would just love them from afar.

Very very far.

Because distance really did make the heart grow fonder in this case.

Now he was finally facing one of his childhood tormentors again. One whom he had luckily gone eight years without seeing.

That was two years more away from Gabriel than he had spent from the rest of his brothers. And knowing that Michael was near by and still in contact with Gabe to some degree sent a shiver of fear down Castiel's spine. The only thing that trumped his fear of Michael, was his fear of Michael reading the email Gabriel had managed to find. It didn't matter how far Castiel ran if that happened. Michael would hunt him down and kill him if he thought his baby brother was tarnishing their father's good name.

Castiel pulled his hanky out of his pocket, blowing his nose on it as he went down the exit ramp from the plane. This was exactly why he hated traveling by air. Hundreds of people confined to a giant metal tube, all breathing the same air. Only this time, Castiel was the sick one infecting them all, but he wasn't really given much of a choice.

Gabriel had only given him the weekend to pack up, set his affairs in order, find someone to watch his cat (because he refused to leave it in a kennel for that long), and tell the post man and neighbor that he wouldn't be there for who knew how long. Then he jumped right onto a plane and was heading out to New York. A city he hadn't planned on revisiting until death, where his family would more than likely drag his rotting flesh to stuff him into some pine box, or incinerate his remains. Not like they hadn't tried to do both at some point already, though it wasn't something Castiel liked to think about. In fact, those few girls he was able to keep the interest of through his college years were all under the impression he was an orphan.

Castiel steeled himself, walking to the baggage claim, finding his luggage, then turning to leave.

He hadn't seen his brother in years. Part of him was wondering if he would even recognize the other man. Another part of him wondered if Gabriel was actually telling the truth for once when he said he would be waiting to for him.

Cautiously, Castiel scanned the yard, looking for the hulking figure of his memories that use to hold his scrawny twelve year old self down to pour hot sauce down his throat and rubbing what bubbled out of his mouth into the skin of his chest, causing it to burn. He looked for that mischievous grin that always meant Castiel was in over his head with something, and Gabriel was going to sit back and enjoy the show. The honey brown hair. The dark brown eyes that were always laughing, even in the worst situations.

Castiel stepped outside of the airport, looking around at the crowd. On the left, he had a mother being taken out at the knees by a hug from what he suspected was her child, and the grandparents that might have been babysitting were standing by, watching with a fond eye. A little ways away from that, a man was passionately kissing a beautiful woman like he hadn't seen her in years. All over the place were similar scenes playing out, and, not for the first time in his life, Castiel wished he had a normal brother that he could greet and hug and be happy over.

"Sorry, but I'm not about to have a sappy, kiss fest like all these yahoos," a snarky voice joked behind Castiel, and he wondered how his brother had snuck up behind him without his noticing.

Then he turned around and couldn't contain the laugh that awkwardly bubbled up his throat. Because it was obvious how Gabe literally snuck under his radar. Gabriel, the person he occasionally still had nightmares about from his childhood, was now several inches shorter than him. He looked just like he use to, other than the slightly longer hair, and he was over all much smaller all around than remembered, considering Castiel hadn't finished his growth spurt before Gabriel left. And to think he was once afraid of the other man.

Of course, Castiel wasn't the vengeful sort, especially seeing as how Gabe had a load of dirt on him. So, he hid his laugh as a cough behind a closed fist, and moved forward to shake his brother's hand.

Gabriel, just as energetic and boisterous as he remembered him being, ignored the hand and went in for the hug, knocking the air out of his chest when he all but tackled him. "Little bro! Your all grown up," he said in a mockingly proud voice, pulling away from Castiel's chest a little to wipe a fake tear from his eye while the other arm remained, locking Castiel in place next to his brother.

"And I see you haven't." Castiel stated blandly, patting Gabriel's back in hopes the other man would let go. They were starting to attract attention, and Castiel pretended to smile when a woman gave him a strange look.

Castiel was just about to open his mouth and tell the woman this was his brother, because from the way she was glaring disapprovingly at him she obviously mistook them for lovers, when, in a flurry of movement, he found himself bent over with his head locked in place beneath Gabriel's arm. If that wasn't embarrassing enough, Gabriel began knuckling him painfully on the head, laughing.

"Gabe!" Castiel growled, fighting the hand around his neck and batting away the fist that was rubbing his hair into a mess and making knots on his head.

Gabriel laughed as Castiel struggled in his hold. "I may be shorter than you, but I am still your big brother. Remember that!" He crowed before pushing a suspiciously wet pinky into his ear, making Castiel squak indignantly.

Castiel finally forced his way out of his brother's hold, trying to straiten his rumpled coat and flatten down his hair, eyeing the onlookers with a narrowed eye, as if daring any of them to mock him for getting manhandled by the shorter man.

All of them quickly looked away.

"You owe me a bottle of cough syrup," Castiel bit out, looking down at his older brother with a scowl. "Security confiscated mine."

"Awe, did those germy little brats get you sick?" Gabriel joked, grabbing one of Castiel's bags (the lighter one, of course), before heading to the parking lot with a hesitant Castiel trailing after.

Gabriel babbled as they walked, about nothing and everything at the same time, while Castiel tuned him out. Congestion and the constant buzzing of chatter was giving him a headache. When they stopped in front of a bright red corvette with it's top down that more than likely cost more than Castiel would make in his entire life, he was sure it was just so Gabriel could make some crude comment about how many girls he could pick up if he owned it.

He was then shocked when Gabriel actually stopped talking for once when he pulled out the keys and unlocked the car, tossing the bag into the back with a flick of his wrist. "I thought you said you were a corporate headhunter?"

Gabriel nodded, obviously not hearing him, before motioning for Castiel to throw his stuff in the back before bypassing the door and jumping into the driver's seat, winking at a random girl that passed by like he was some kind of a movie star. "What?" Gabriel called back to him absently when the girl winked back and blew him a kiss.

Castiel rolled his eyes, picked up his suitcase and threw it in the back a little harder than was necessary, hoping that he caused some harm to the leather. He shook his head when not even that shocked his brother out of his attempt at charming a girl from across the parking lot now. He opened the door and climbed in, ignoring just how out of place he felt in this environment. Then he remembered he would be working for a big lawyer firm for the next several weeks, so he might as well try to get use to it now. He remembered just how overwhelming his father's law firm had been from the hand full of times he was able to visit it when he was a child.

After slumming it and eating nothing but ramen in college to save up so he didn't have to come running to Michael for a bailout, he was use to living within his means. That meant the basic channels on tv, a roughly used car, and up till recently, a cheep flip phone. Obviously he shouldn't have switched over considering Gabriel was able to find him with it, but he thought he deserved something nice for once. He had only recently moved to a nicer part of the neighborhood back home, and his apartment now had one and a half bathrooms, and he wasn't forced to triple lock everything before feeling safe enough to fall asleep at night.

Gabriel patted his knee and shot his brother a soft smile. Castiel's frown deepened. He most certainly never saw that look on his brother's face growing up. It almost looked caring.

"Hey, kid. Really, thanks for doing this for me on such short notice. You really are saving my bacon here," Gabriel said, turning the key in the ignition before setting the car in reverse. "As soon as we get home, it's all the cough syrup you can drink. In fact, I will even pull out the Humidifier," Gabriel said, pulling out of the parking garage, letting Castiel catch his first glimps of the city that wasn't through a plane window. Castiel hated it. In fact, he was so focused on how much he hated the lights, sounds, people and buildings of the big city that he almost didn't catch the, "Promise I won't pee in it this time."

Castiel's jaw tightened and he closed his eyes, taking several measured breaths to calm himself. Because he most certainly did not know Gabriel had done that to him before, and part of him wondered how often when he was sick as a child Gabriel had snuck into his room to pee.

He really hoped not often.

"You can forget the humidifier. I just need a night's sleep."

Gabriel grinned and nodded. "Just don't sleep too late! You start tomorrow at noon sharp over there."

Castiel followed where Gabriel's finger was pointing, straight at a ornate, expensive looking high-rise office building. He felt like he was going to be sick, and it had nothing to do with the fact he really was sick. In less than 24 hours he would be standing in the shadow of that building, at the mercy of people with more money and power than he cared to think about, who could possibly ruin his life worse than Gabriel's threat.

And he had no clue what a secretary even did. What if he pissed someone off? What if he pissed a lawyer off?!

This was going to be just great.

* * *

Dean had been avoiding his little brother like crazy all last week, and even over the weekend. This week, however, he didn't really give a crap. The world was a better place now that he had a secretary. It was Monday, a new day and a new work week. Things were going to be great.

The moment he stepped off of the elevator, he grinned at Sam, who had been waiting to attack him with his rumpled bitch face on.

"Dean, you need to stop telling Meg to prioritize your stuff over mine! She is my secretary!" Sam complained the moment he stepped off of the elevator and began walking to his office.

Dean just smirked, "Won't be a problem anymore, Sammy!"

Sam actually tripped over his ridiculously big feet in his tracks he was so shocked at the statement. "Wait, Gabe finally found you a new secretary? This soon? It's only been a week!"

Dean flashed his brother one of his famous, case winning smirks while he kicked his door open and went inside. "By noon time today, I will have a new, hot little thing sitting right there," he pointed to the desk they had passed to get to the door to his office, "and she will handle all of my needs, instead of your demonic little secretary." Dean leaned against the doorway to his office, happily enjoying the look of shock that his brother was making.

"Wait, how did you get him to find you someone so fast? When Ruby left and I had to find someone else it took him a month to find Meg!"

Dean shrugged, "I was persistent," he preened.

Sam's face fell for a moment, before it was replaced with an amused grin.

"Oh no!" Sam chuckled. "How persistent were you?! Please tell me you didn't threaten Gabe to get a secretary faster than usual!"

Dean's brow furrowed. He frowned. "Maybe a little, but I was stressed!" He defended. "I apologized."

"Did you apologize before or after he found you a new secretary?" Sam said, getting more and more amused, and Dean didn't know why.

He at least had enough decency to look ashamed before admitting, "Um… after." He mumbled, scratching the back of his neck nervously when his brother burst into laughter. "What?!"

"You know Crowley, right?"

Dean nodded. It was hard not to know Crowley in this city. The man owned the building, and several others just like it in town.

"He pulled the same thing with Gabriel, and ended up with some, and I quote- 'incompetent, saggy titted cow that was older than God himself.'"

Dean stood there for a moment, his good mood fading rapidly. "Shit!"

Dean turned and began pacing his room. He tried to slam the door after him, but Sam blocked it with his foot. "What is her name?"

Dean stopped his frantic pacing. "Cas-something. I don't remember. It sounds kinda foreign, and, until now, I thought it was pretty hot."

Sam started laughing again, "Hey, maybe she is still a hot little thing! Maybe she just doesn't know a lick of English."

Dean groaned. That would be his luck, wouldn't it?

Sam patted his brother's shoulder consolingly. "Look, as much as I would love to hang around here and comfort you, there are two hours till noon, and I need to make my rounds."

Dean shot a deadly glare at his little brother. "You wouldn't dare!" He hissed.

"Hey! You know the rules. I'm just going to take an office pool of how old they all think she will be. Maybe we will place bets on what will be wrong with her."

Dean scowled at his little brother, pulling out his wallet. He pressed a fifty into his brother's hand. "I want in on the action."

Sam's brows rose, "Oh really? What do you want to place your money on."

Dean groaned, running a hand down his face. "Call me optimistic, but I will bet against all of you in hopes that she will be my age or younger. And hot."

Sam grinned, and looked down at the fifty in his hands. "Thanks for the donation!" And with that, he loped out of the office, heading straight for the main desk where a group of staff was congregating.

Dean groaned before walking around his desk and sitting down heavily in his chair. This was going to be a long day. And the thought that he may or may not have jerked off to the image he painted of his new secretary over the weekend more than once made him want to puke a little.

He really, really hoped his brother was wrong about this, because if he wasn't, there wasn't enough bleach in the world to purge the thought of screwing some old lady from his mind. And once he met his new secretary, he would instantly rethink all of those dirty thoughts he had about them with an actual face to put to the imaginings, whether he wanted to or not. And if it was some motherly, or, God forbid, grandmotherly figure he ended up with… he didn't think he would be able to keep his breakfast down.

He was more disgusted with himself than the secretary he was about to meet. It wasn't her fault that the porn industry had so many sexy teacher themes. It wasn't her fault that his mind instantly went in that direction when he heard about her.

The thought of screwing his new secretary against a blackboard or school desk had the opposite reaction it previously had on his dick not two nights ago. Part of him wondered if he would ever be able to get it up again.

He really hoped Sam was wrong about this one. He really, really did.

* * *

Sam was enjoying the bets he had collected so far. Everyone was getting in on the action, and they all had been amazingly creative about the outcome. Ash, the head of the IT department, placed his bet on her being really, really old. 'Like, with blue hair and dentures, old!' Bobby, amusingly enough, bet she would be in a wheelchair. Their father even wanted in on the action, deciding that he liked the idea that she would be unable to speak English. Charlie threw a few bills at him, stating the new girl would be a lesbian. Sam decided that he would change up his bet, because he suddenly found the idea of the new secretary being happily married hilarious, especially with how Dean had a tendency to sleep his way through the entire city during a hard case, 'to keep the creative juices flowing.'

Several more people threw a few bills into the pool, all of them sticking with the options listed, all equally amused at the thought of his pigheaded, overly zealous brother getting one pulled over on him for once. Because very few people had the balls to stand up to Dean Winchester, and if Gabriel decided to put Dean in his place? Nobody was going to complain about it. Nobody at all.

Sam counted out the money, passing it over to Meg, along with the slip of paper with the bets on it. She accepted it with a lopsided grin that had the tendency to make many people uncomfortable. "All done?" She asked, placing it all in an envelope without looking at it, then setting it gingerly to the side.

Sam nodded eagerly. "You never placed a bet of your own. What do _you_ think it's going to be?"

Meg laughed, a sound that was rather hollow. "Sammy, you know how I feel about gambling," she said with a shake of her finger in the youngest Winchester's direction. "I only do it if I know I am going to win," she joked. Or, Sam was pretty sure she was joking. He never really could tell. "Though, I rather like Bobby's dark humor. It would be priceless if she were paralyzed from the waist down. It would be a million times more hilarious if it was all of the bets combined."

Sam forced himself to laugh at that. Meg always had a dark sense of humor. That was part of why Sam liked her as his secretary. As Dean liked to put it, Sam had a tendency to be a little too kind, so having a skull and crossbones kind of secretary helped to keep clients and opposing counsel from walking all over him.

Sam leaned over the desk to tell her his own conspiracy theory about the new secretary when a rather lost looking man stepped into the office, looking around the room like he had never seen the inside of a building before. When he caught sight of Sam leaning up against the desk, and Meg eyeing him up and down like a cat readying to pounce on a mouse, he nervously walked over to them, his worn briefcase in hand, and a rumpled tan overcoat folded over his arm.

He looked like he was about to ask something, but just as the words were about to come out of his mouth, Sam pushed himself away from the desk, now standing at his full height. Despite the fact that Sam was grinning politely at the newcomer, the man snapped his mouth shut and visibly swallowed back his words. It wasn't an uncommon response where Sam was concerned. He was about half a foot taller than the man, who was in no way short himself, and to people that didn't know him, he _was_ fairly intimidating.

The man's blue eyes widened momentarily, before schooling his features as he once again looked around the room, nervously loosening his tie. The man looked a rumpled mess of nerves. His hair was wild, making him look like he had been running his hand through it all day, and his brow was almost permanently furrowed with a look of innocent confusion, as though someone just told him wrestling wasn't real, or unicorns didn't exist.

He opened his mouth again while looking at a strange, abstract painting hanging on the wall, obviously to uncomfortable to say whatever he was thinking while making eye contact.

Sam's first thought was that he was someone's client. And by the state of his partially stubbled chin, crooked tie, and slightly wrinkled suit, Sam suspected he was going through divorce proceedings. No self respecting wife would let a man leave the house looking like that. He continued to observe the odd man's behavior, leaning against the desk to make himself look a little shorter and less imposing to the stranger while picking up an unattended mug of coffee behind him, blowing on it a little before taking a sip. He decided that it would be best to let Meg deal with this one.

Meg knowingly took the lead that Sam gave her, and broke the awkward silence. "Is there something I can help you with, dear?" She said in an overly sugary tone that caused Sam to do a double take. Was she flirting with this bag of insecurities? Really?

The man cleared his throat, before looking in her direction, brows furrowing even deeper at her question, lips parting a little as a deeply pained look crossed his rather chiseled features, like he was being held at gunpoint and would rather be anywhere else at the moment. Even Sam had to admit that, while this man was obviously a bit lost at the moment, he could understand why Meg would be interested in him. He was somewhat attractive.

Then the stranger opened his mouth.

"I believe so," he stated in a deep, booming monotone that really didn't match the rest of his being. It was the kind of a voice that most people would expect to come out of someone Sam's size. That, or a body builder. It was deep, husky, and suggested something of a sexual nature. Which then made his ruffled suit and messy hair give off less of a homeless man vibe now, and more of a "I just had wild, crazy sex in that closet over there," vibe.

Sam just looked at the man over his nearly forgotten cup of coffee, dumbfounded at the sudden change, while Meg's smile grew down right predatory.

It would be just like Meg to go after a recently divorced man. She seemed to love broken people, and always enjoyed toying with the depressed drunks at the bars when Sam took her out for victory shots. Sam was just happy he had a tendency to be a happy drunk during those situations.

"Well, just tell me who you are here for, and I will point you in the right direction, darling," she cooed in a babyish voice that she tended to reserve for clients who needed the extra little push in the right direction. Sam suspected she thought it sounded sexy, but in reality it was downright patronizing.

It obviously didn't work on this man. His face remained the same confused scowl, but this time it was directed at her instead of the wall. "I am Castiel Novak, and I am supposed to meet a…" he pulled out a note from his pocket, which looked to be typed out on some official looking stationary, "Dean Winchester?" He read the name from the page as though he had never spoken it before that very moment in time.

"Did you have an appointment with him?" Meg asked in a patient, almost sickeningly sweet voice. "We recently had a problem with our scheduling, and the book that held your appointment with mister Dean Winchester was temporarily misplaced. If you did have a meeting with him, I am sorry to say that we may have to reschedule it for a later date."

Castiel tilted his head to the side, as though Meg just uttered something in a completely different language than he was use to. "I was already informed of said dilemma," he rasped, as though it was common knowledge Becky ran off with the date book and the mail room guy.

It was Meg's turn to furrow her brow. "Dean didn't tell me he scheduled any meetings with clients today."

The man was carefully eyeing up Sam again at that point, uncaring, or just oblivious to the fact that Sam was doing the exact same thing back. Meg seemed more than a little irritated at the fact he was no longer paying her any mind.

"Perhaps if you could tell me what your meeting with Dean was about, I could call him up and see if he would be willing to meet with you today?" she asked somewhat impatiently.

The corners of the man's lips quirked slightly. "I don't know why Dean wouldn't tell you about my arrival, nor why he would refuse to meet with me," the man said, running his hand through his hair, making him look more even disheveled and confused than before.

Sam took a long gulp of his cooled coffee.

"I was sent here by Gabriel," he stated after a silence as awkward as the man himself was. As though what he said was the most obvious thing in the world.

There was another moment of silence as they tried to make sense of the words coming out of the strange man's mouth. Meg and Sam turned to each other, somewhat lost as to why Gabriel would be sending them this strange little man. They simultaneously turned back to the man, who's brow was twitching irritatedly.

"Gabriel did inform you of my arrival, did he not?" His brows furrowed again, though this time it was less of an innocently confused expression, and much more of a murderous one. The way he spat out Gabriel's name suggested who would be on the other end of the gun later.

Sam shook his head. "Not that I can recall."

The man's hand went to pinch the bridge of his nose, obvious irritation pulsing off of him in waves. "I swear…" he muttered under his breath.

Sam watched the man's breakdown with bareley restrained amusement, taking another sip of his coffee, and Meg seemed to second his amusement, chuckling softly to herself behind Sam.

The man took several deep breaths before pulling out of it to address the two before him. "Obviously there was some form of... miscommunication," he ground out. He turned to leave, making his way to the door while stating casually over his shoulder as he went, "I was misinformed that Dean Winchester was in need of a secretary for a few months."

That statement alone was enough to make Sam choke on half a gulp of his coffee, spraying the other half across the room while trying to clear his windpipes. Meg instantly stood, hitting Sam on the back in an attempt to revive him… or maybe she was just hitting him for the fun of it. Once again, Sam couldn't really tell for sure.

"If that is not the case," the man continued, so blinded by his rage that he didn't even take note of the fact Sam was practically dying behind him. "I will see myself out. I apologize for the interruption. I will make sure Gabriel pays for both your waisted time, and my own."

The man was probably half way to the elevator by the time Sam recovered. Instead of choking, he was now spluttering in laughter.

"Should I go after him?" Meg asked, eyeing her boss as though the thought of him dying in front of her was a dream come true, but she would be out a good paying job if he really did kick the bucket, and she wasn't really sure which one she wanted more.

Sam nodded, trying to catch his breath while Meg quickly stepped out of the room to catch the other secretary before he could leave the building.

This was better than everything he and the betting pool had come up with combined.

He couldn't wait to see Dean's face when he found out his new secretary was actually a guy.

Gabriel was a genius.

Sam quickly took off in the direction of his brother's office, grabbing the envelope of money as he went.

This was going to be priceless.

* * *

Dean was slightly baffled when his brother strode into the room with a blinding grin distorting his features just before Dean's fifty dollar note fluttered down to the desk in front of him. He checked the time. It was a little after noon.

"Was I right? Is she a hot young thing?" Dean asked in shock as he looked down at the bill.

Sam laughed harder than Dean had heard in a long time, and instantly his hoped was dashed. "No. I was forced to redistribute the betting money, considering nobody guessed it correctly."

Dean's heart dropped. Sam flopped lazily into the seat across from his brother, slouching so he could get comfortable, his long, gangly legs taking up most of the space in the office before he kicked them up onto his brother's desk, earning him another dark glare.

Dean took a deep breath, trying to steal himself for the big reveal.

"Well, what is it? What's wrong with her? Tell me now so I don't end up gawking at her when she finally walks through the door."

Sam grinned. "Oh, I don't think so Dean. It's supposed to be a surprise. I would hate to ruin it."

Dean scowled. "Where is she?"

"Your new secretary will be here in just a moment. Meg had to chase them down."

Dean frowned in confusion. He was just about to start cursing his little brother, when the door to his office swung open, and Meg all but pushed a harried looking man into the room. He tripped on the edge of one of the chairs rather ungracefully, only to catch himself across Sam's outstretched legs.

"My apologies," the man muttered in an impossibly deep voice before quickly pushing himself back into a standing position. His face was flushed, and he was seemingly out of breath, as though Meg had been running him straight there from the elevator. Which she probably had.

The man attempted to right himself, adjusting his tie, running one hand through his hair and the other over his suit in an attempt to dewrinkle it while simultaneously wiping the sweat from his palms off on the fabric. He turned to face Dean, and an unnatural, fake smile was forced onto the man's obviously nervous features. Every correction the man had made to his appearance only seemed to backfire. The tie was now more crooked, nearly backwards and was now more around his neck like a noose rather than under his collar like it should have been. His hair was also impossibly tussled, and his suit looked as though he had been wearing it for two days straight. Even the man's palm was uncomfortably clammy when he thrust it into Dean's face to shake.

For some strange reason, Dean didn't seem to notice any of that. Or, while he did notice that and internally cringe at the man's pitiful demeanor, it all seemed to fade into the background when his eyes met the other man's deep blue eyes. They were the kind of eyes he would have loved to see on a girl. The kind of eyes he could drown in before he attempted mouth to mouth with those perfectly shaped Cupid bow lips.

Dean shook himself out of that thought, mildly aware that the other man had said something while he had been shaking Dean's hand.

"I beg your pardon?" Dean said, pulling himself out of his thoughts long enough to form a few intelligible words. He forced a friendly smile onto his face to put the man at ease, glancing behind the stranger and at the door, slightly confused by the fact nobody else was coming through it.

That deep, raspy voice brought his attention back to the man in front of him. Wow. That voice really didn't match that man's body. God must have been having fun when he was making this guy.

"I said, my name is Castiel Novak."

And his father really must have been having a good laugh when he named him. Castiel? Sounded like a girl's name.

Dean's mind suddenly froze.

In fact, didn't his new secretary have that exact name?

Dean forced himself to smile, and avoid thinking about the many fantasies he had while screaming this… man's name.

"It's," he coughed into his hand, using the motion to simultaneously pull his hand out of the other man's still pumping one, and use the action to buy him some time while clearing his mind, "wonderful to finally meet you!" He finished with forced enthusiasm.

It must have been obvious that Dean was forcing it, because the man cocked his head at the sight like a curious dog.

Dean stood from the desk, straightening his suit jacket and trying to collect himself. His eyes locked with Meg, who was beaming at the barely concealed look of horror on Dean's face.

Dean quickly pointed at her, averting the man– Castiel's, attention in that direction.

"Why don't you follow Meg, and she will get you settled at your desk and show you the ropes," Dean said, scrambling to find some way to get out of this awkward moment. He had jacked off to this guy, thinking he was a girl!

Suddenly an unbidden image of him pounding the guy over his desk crept to the forefront of his mind, making him splutter. When Castiel turned those soulful blue eyes back in his direction in worry, Dean quickly covered it with a fake cough before quickly taking his seat again and crossing his legs to hide his growing problem. Horrifyingly enough, he apparently could get it up again. His body certainly had a sick sense of timing and humor.

"Sam and I have some important matters to discuss," he covered quickly, trying to look professional by folding his hands over the spread sheets scattered across his desk in an organized mess. "Shouldn't be too long, and after we are through I will come and see how you are adjusting."

Castiel nodded quickly before making his way out of the door, tripping over the furniture again as he went.

Meg waited for Castiel to step out of the door before following after, only pausing a moment before looking in Dean's direction before pointing at Castiel's retreating figure, though pointing a little downward. She mouthed words that suspiciously looked like, "that ass!" before stalking after his oblivious new secretary with a never before seen leer plastered to her face.

When the door closed, he looked over at Sam, who's features were even more frightening than Meg's had been. He looked like he was about to laugh his ass off.

Dean gripped his forehead, trying to wish this all away. This was going to be the longest month ever.

Then he remembered something and grinned. "Hey Sam?"

"What Dean? Enjoying the sight of your new office slave?"

That was not a good comparison for Dean's mind right now, especially considering the direction his brain was taking it. It was the same direction his head went when he was informed that his new secretary was a school teacher. Now he was just thinking of those innocent blue eyes looking up at him in fear while the man was forced on bended knees, wearing little more than shackles and a loincloth while Dean towered over him with a whip—

 _No!_ Dean didn't do that kinda shit with a guy! And if he ever did, then he was so drunk that he would never admit to it.

Dean shook the thought from his head with a smile. "I was right in a way. He is attractive and around my age. I am pretty sure that means I win the whole jackpot," Dean tried with a weak smile, only partially joking.

Sam laughed at that before standing. "You said 'she.' That in there is obviously not a she, and if it is, you are going to have to get me some concrete evidence. Until then, I have some money to redistribute, and a case I have been neglecting. I'm pretty sure you have a case to work, too."

Sam stood and walked out of Dean's office with a cocky swagger as Dean eyed the suspiciously full envelope with sad eyes. That would have been a really nice bonus.

"Don't worry about your precious little secretary. Meg will have him all trained up before the end of the day to be the perfect little lapdog for you," Sam teased one last time before shutting the door behind him.

Dean opened his case file with a frown, trying to force the unbidden imagery of his new secretary with dog ears, a tail, and a leash wrapped around his neck out of his extremely active imagination.

He slammed the folder shut again, when his mind wandered to Castiel panting like a dog for different reasons.

He really hoped the day would pass quickly so he could hit the bar. His overactive libido needed to cool it. He wouldn't be able to get any work done like this!

When was the last time he got laid anyway?

* * *

Once again, this story is a chickengoesmoo work, and I own nothing. If you wish to read more of my work, come check it out at ChickenGoesMoo, at Archive of our own.


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